Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
  • C08G59/72—Complexes of boron halides
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/14—Polycondensates modified by chemical after-treatment
  • C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
  • C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
  • C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
  • C08G59/1461—Unsaturated monoacids

Definitions

• a plurality of coatings. of this composition may be applied to an object at any desirable interval without any danger of the previously applied coatings lifting or dissolving,
• Patent 2,596,737 discloses one particular process for reacting similar ingredients.
• the coating compositions produced in accordance with that patent cannot be superimposed safely unless the previous coatings have been quite completely cured by prolonged heating or"air drying. Otherwise, a subsequently applied coating will lift the coating beneath it and producedefective coatings.
• a coating of a composition prepared in accordance with that patent is applied to a surface and dried for 4 to 8 hours, and is then painted over with another coating of the same composition, the lowermost coating will lift and consequently the entire application of the two, coatings becomes inferior and is defective.
• the object of this invention is to provide for reacting an olefinically unsaturated aromatic compound and olefinically unsaturated fattyacid and an epoxide resin in a particular manner to produce a coating composition that will not lift when applied as a plurality of coatings on.
• Particularly suitable olefinically unsaturated aromatic compounds are aryl alkylene compounds such as monostyrene, alpha methylstyrene, paramethylstyrene and 3-monochlorostyrene, and mixtures of two or more.
• the amount of the unsaturated. aromatic compound should be suflicient to provide less than 2 but more than 1 olefinic groups per olefinic group in the fatty acid.
• the refluxing is carried out for at least /2 hour longer; The refluxing may be 'carried out for 2 or more hours after completing the addition of the unsaturated aromatic compound.
• a resinous epoxide which'comprises. a polyether having alternating glyceryl radicals and hydrocarbon radicals derived from a phenol united .in .a chain by ether oxygen atoms and with hydroxyl radicals present.
• the quantity of the resinous epoxide added should be sufl icient to provide substantially 1 hydroxyl radical per carboxyl group in the unsaturated fatty acid. It is preferable to have a slight excess of the hydroxyl groupsover the carboxyl groups.
• the reaction vessel is heated from a temperature of C. to 250 C. or even higher for a period of time corresponding to approximately 1 hour at230 C.
• the unsaturated fattyfacids employed in practicing the invention should have at least 12' carbon atomsfa nd have an iodine value of over 110 up to 400. Theremay be employed either a single unsaturated fatty acid or mixtures of two or more. Examples of suitable fatty acids are linseed oil fatty acids, linoleic acid, dehydrated castor oil, cottonseed oil acid. hemp'seed oil acids, and dimerized linoleic acid.
• the resinous epoxide to be employed in the practice of the invention is preferably one prepared from reacting from 1.1 to 1:5 ,moles of epichlorhydrin for, each mole of bisphenolbis(hydroxyphenyl)dimethylmethane.
• a par: ticularly suitable resinous epoxide is one produced by ireacting 1.25 moles of epichlorhydrin with one mole' of bis(4-hydroxyphenyl)-2,2-propane to a, resin.
• the epoxide equivalent is the grams of resin containingone epoxy grQ P,. and the equivalent weight is the grams of resin required to e sterify Patented Oct. 20,1959
• Example I Into a reaction vessel there was charged 200 parts by weight of linseed oil fatty acids comprising approximately 45% by weight of linolenic acid, 25% linoleic acid and 20% oleic acid, the fatty acid having approximately 2 olefinic groups per molecule.
• the stirrer of the reaction vessel was put into operation and carbon dioxide gas was employed to sparge the vessel.
• the fatty acid in the vessel was heated to a temperature between 180 C. and 190 C. and 200 parts by weight of monostyrene were introduced slowly over a period of three hours. Refluxing was employed throughout the addition of the monosytrene.
• the resinous reaction product of this example was dissolved in xylol to produce a 50% solution. Coatings of the solution applied to surfaces as a film 3 mils thick air dried tack free in approximately minutes. Panels were coated with the solution of this example and were dried for various periods of time. A second coating was applied to the panels at the end of 2, 4, 8, 16, 24 and 48 hours, respectively. In no case did any of the coatings lift or otherwise sulfer upon the application of the second coatings of the same composition.
• Example 111 The process of Example 'I was modified by substituting vinyltoluene in place of the monostyrene.
• the resulting resinous reaction product had a final reaction value of 6.6 and a viscosity of H when dissolved to produce a 50% solution in xylol.
• the air drying time to produce a 3 mil thick tack free film was 10 minutes.
• Example IV The reaction of Example I was followed except that the fatty acids comprised a mixture of equal parts by weight of rosin acids and linseed oil fatty acids.
• the acid value of the resinous composition was 9 and the viscosity of a 50% solution in xylol was L.
• the composition produced a 3 mil thick tack free film upon air drying for 10 minutes.
• compositions of the present invention may be modified by substituting for a portion of the unsaturated aromatic compound up to by weight of acrylonitrile.
• the following example illustrates this feature of the invention:
• Example V The process of Example I was followed with the exception that 180 parts by weight of monostyrene and 20 parts by weight of acrylonitrile were mixed. Otherwise, the reaction is identical to that in Example I.
• the acid value of the final resinous reaction product was 2.8 and the viscosity of a 50% solution in xylol was X. A three mil thick film air dried tack free in 10 minutes.
• Coatings of the composition of this Example V were found to be non-lifting when tested under the conditions set forth in Example I. Coatings of the composition of this Example V containing acrylonitrile were found to have a greatly improved arc resistance. Thus, where the arc resistance of the composition of Example I was to seconds, the arc resistance coatings of this Example V were 220 seconds.
• Example VI The process of Example I was followed with the exception that there were employed 180 parts by weight of linseed oil fatty acids and 20 parts by weight of dilinoleic acid.
• the acid value of the final composition was 3.5 and the viscosity of a 50% solution in xylol was V. Films of a thickness of 3 mils air dried tack free in 10 minutes.
• the resins of the present invention are compatible with and can be blended with urea-aldehyde and melamine aldehyde resins.
• 100 parts by weight of the resin of Example I may be mixed up to 60 parts by weight of either butylated urea formaldehyde resin or melamine formaldehyde resin and the mixtures dissolved in a solvent thereby producing a coating composition.
• a coating composition was prepared from 75% by weight of the resin of Example I and 25 parts by weight of solvent soluble butylated formaldehyde resin, all dissolved in xylol. Coatings of this mixed composition were applied to metal and glass bases. These films possessed excellent mar and scutf resistance. These compositions resisted lifting upon being recoated.
• compositions are prepared by reacting, as described herein, 100 parts by weight of monostyrene to from 80 to parts by weight of linseed oil fatty acids and after such addition the resinous epoxide is added in an amount from 125 to parts by weight, the epoxide having an equivalent weight of approximately 175 and an epoxide equivalent of approximately 950. Resins prepared from these proportions reacted in the order and manner as heretofore set forth are non-lifting when recoated.
• Pigments such as iron oxide, titanium dioxide, carbon black and zinc chromate and fillers such as silica and dyes may be incorporated in the composition. Coatings of the compositions may be baked or air dried. In either case, the films have excellent Water and alkali resistance.
• the unsaturated fatty acid being refluxed during the addition of the unsaturated aromatic compound, the amount of the unsaturated aromatic compound added being sufficient to provide for from less than 2 to more than 1 olefim'c group therefrom for each olefinic group in the unsaturated fatty acid, refiuxing being carried out for at least approximately /2 hour to several hours after the required amount of the aromatic compound has been added, thereafter admixing with the resulting reaction product a resinous epoxide com- AIL m prising a polyether having alternating glyceryl radicals and the hydrocarbon radicals of a phenol united in a chain by ether oxygen atoms and with hydroxyl radicals present therein, the resinous epoxide having an equivalent weight of approximately 175 and an epoxide equivalent of from 900 to 1000, the resinous epoxide being added in an amount to provide substantially one hydroxyl radical per carboxyl group in the unsaturated fatty acid, and heating the mixture at
• the unsaturated fatty acid being refluxed during the addition of the unsaturated aromatic compound, the amount of the unsaturated aromatic compound added being suflicient to provide for from less than 2 to more than 1 olefinic group therefrom for each olefinic group in the unsaturated fatty acid, refluxing being carried out for at least approximately A2 hour to several hours after the required amount of the aromatic compound has been added, thereafter admixing with the resulting reaction product a resinous epoxide comprising a polyether having alternating glyceryl radicals and the hydrocarbon radicals of a phenol united in a chain by ether oxygen atoms and with hydroxyl radicals present therein, the resinous epoxide having an equivalent weight of approximately 175 and an epoxide equivalent of from 900 to 1000, the resinous epoxide being added in an amount to provide substantially one hydroxyl radical per carboxyl group in the unsaturated fatty acid, and heating the mixture at a temperature of from 190 C
• a resinous reaction product derived by slowly introducing over a period of at least an hour 100 parts by weight of monostyrene into from 80 to'150 parts by weight of linseed oil fatty acids, the fatty acids being maintained at a temperature of from 150 C. to 220 C. and being refluxed during the addition of the monostyrene, refiuxing being carried out for at least approximately /2 hour to several hours after the monostyrene has been added, thereafter admixing with the resulting reaction product to 175 parts by weight of a resinous epoxide having an equivalent weight of approximately 175 and an epoxide equivalent of 950, and heating the mixture at a temperature of from 190 C. to 250 C. for a period of time until there is produced a resinous composition of an acid number of below 15 and which is soluble in xylol.
• the unsaturated fatty acid being refluxed during the addition of the unsaturated aromatic compound, the amount of the unsaturated aromatic compound added being sufficient to provide for from less than 2 to more than 1 olefinic group therefrom for each olefinic group in the unsaturated fatty acid, refluxing being carried out for at least approximately /2 hour to several hours after the required amount of the aromatic compound has been added, thereafter admixing with the resulting reaction product a resinous epoxide comprising a polyether having alternating glyceryl radicals and the hydrocarbon radicals of a phenol united in a chain by ether oxygen atoms and with hydroxyl radicals present therein, the resinous epoxide having an equivalent weight of approximately and an epoxide equivalent of from 900 to 1000, the resinous epoxide being added in an amount to provide substantally one hydroxyl radical per carboxyl group in the unsaturated fatty acid, and heating the mixture at a temperature of from C.

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• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Emergency Medicine (AREA)
• General Chemical & Material Sciences (AREA)
• Paints Or Removers (AREA)
• Epoxy Resins (AREA)

Priority Applications (4)

Applications Claiming Priority (1)

Publications (1)

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Family Applications (1)

Country Status (3)

Cited By (4)

Citations (6)

• 0
  • BE BE530542D patent/BE530542A/xx unknown
  • BE BE530543D patent/BE530543A/xx unknown
• 1953
  • 1953-07-21 US US369518A patent/US2909497A/en not_active Expired - Lifetime
• 1954
  • 1954-07-19 FR FR1110821D patent/FR1110821A/fr not_active Expired

Patent Citations (6)

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